When life gets confusing and leaves us in binds, we look to our close friends for help. The biggest dilemma that strikes many men is how to pair their outfit with apt shoes. Even with an active stylist’s team working to get you all the right things, there’s always a chance you might be committing the proverbial sin of a fashion faux pas. And when it comes to formal shoes for men, the stakes are stacked even higher. But fret not; just like a trusted friend, you can depend on a pair of classic Derby shoes to help you walk the talk with a little more style.

If you’re new to the Derby scene, let us give you a bit of introduction. Under the gamut of formal shoes, Derby is one pair that is often confused with the Oxford shoes, due to their elegant design and look. However, their distinctive lacing systems set them apart. Derby shoes have an open lacing system as opposed to the closed lacing of the oxford. The quarters with shoelace eyelets of the Derby are sewn on top of the vamp, giving it a more casual look than tight-laced oxford, and still maintaining a formal vibe.

Sometimes relegated to a side player in the game of shoes, a Derby is the subtle wingman that can make any outfit look good. It looks smart enough to impress your date and her Nan, and has that casual vibe to suit a Sunday stroll across the street. And of course, when it comes to playing the style cards right for the office, you can never go wrong with a slick pair of Derby.

To help you, we’ve curated three best ways to style your outfit with a pair of Derby shoes. Have a look:

Fun with formals

A plain leather Derby in a traditional brown shade should be a mandatory addition to your wardrobe, if it isn’t already. Pair it with a tailored navy suit to turn heads atork. The dark navy looks striking against shades of tan, but if the colour of your suit is light stick to black shoes. Avoid tan-hued Derby with grey outfits, as this would go better when paired with dark brown, cherry red, oxblood or black coloured shoes.

When wearing pinstripes, stick to plain a Derby in classic black/brown colours for a sophisticated look. The stripes already create the drama, so make sure your shoes complement the suit rather than adding more volume to it. Also important to remember is the colour of your belt – it should match the shade of your shoe.

Smart for the streets

Fancy a casual summer party but don’t know what to wear? Try a high-end suave look with your Derby shoes. Pair a brown Derby with off-white tailored pants, topped with a blue V-neck t-shirt/sweater. Dark brown or sand coloured suede Derby shoes are great for casual wears, especially when paired with chinos.

For that smart and sporty look, a pair of black Derby topped with a bomber jacket makes for a dazzling combination. Add in a simple crew neck t-shirt, and wear it with straight-leg formal trousers. With a dash of a tempting perfume, you will be ready to go!

If you’re planning to wear a formal Derby with jeans, make sure you choose the right pair. Distressed jeans, light-coloured or a ripped pair should never be worn with any formal shoe. Instead, opt for dark wash jeans with a tapered fit at the bottom. When wearing Derby shoes, maintain the length of your casual pants that cuts off at the ankle.

Prep for the party

Even for party wear, you do not have to look too far away from your Derby shoes. Their versatility makes them the perfect wingman for all your party outfits. For a stylish yet comfortable look, wear a long gingham shirt with dark coloured jeans over your black pair of Derby shoes. Go for a pair of black socks and cuff your jeans at the bottom – smart and smooth. You can also put on a formal tuxedo jacket over a striking patterned shirt, and pair it with a simple Derby for a clean and edgy look. If you want to skip jackets, then try a plain half-sleeve shirt with tailored trousers and black suspenders. Add a cute bow tie, and further your look with a trendy hat for an effortlessly charming look, if you wish to go bold.